Fellutanine

Fellutanines A,B,C and D

Fellutanine A,[1] B,[1] C and D are bio-active diketopiperazine alkaloids isolated from the cultures of Penicillium fellutanum,[2] that belongs to a class of naturally occurring 2,5-diketopiperazines.[3] Originally they were thought to be based on the "trans" cyclic dipetide cyclo(L-Trp-D-Trp) [2] but were later shown to be based on the "cis" cyclic dipetide cyclo(L-Trp-L-Trp).[4] This was also confirmed when fellutanine A, B and C were isolated from Penicillium simplicissimum.[5] The fellutanines A−C, are non-annulated analogues of cyclo(L-Trp-L-Trp), but unlike their diannulated analogue fellutanine D are not cytotoxic.

References

  1. 1 2 Kozlovsky AG, Vinokurova NG, Adanin VM (2000). "Diketopiperazine alkaloids from the fungus Penicillium piscarium Westling". Prikladnaia biokhimiia i mikrobiologiia. 36 (3): 317–21. PMID 10867952.
  2. 1 2 Kozlovsky AG, Vinokurova NG, Adanin VM, Burkhardt G, Dahse HM, Gräfe U (March 2000). "New diketopiperazine alkaloids from Penicillium fellutanum". Journal of natural products. 63 (5): 698–700. doi:10.1021/np9903853. PMID 10843594.
  3. ↑ Borthwick AD (2012). "2,5-Diketopiperazines: Synthesis, Reactions, Medicinal Chemistry, and Bioactive Natural Products". Chemical Reviews. 112 (7): 3641–3716. doi:10.1021/cr200398y. PMID 22575049.
  4. ↑ Kozlovsky AG, Vinokurova NG, Adanin VM, Burkhardt G, Dahse HM, Gräfe U (2001). "New diketopiperazine alkaloids from Penicillium fellutanum". Journal of natural products. 64 (4): 553–554. doi:10.1021/np010005p.
  5. ↑ Hayashi H (December 2005). "Bioactive alkaloids of fungal origin". Studies in Natural Products Chemistry. 32. Elsevier. pp. 549–609. doi:10.1016/S1572-5995(05)80064-X.


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